Tandem Aza-Wittig/Carbodiimide-Mediated Annulation Applicable to 1,2-Diaza-1,3-dienes for the One-Pot Synthesis of Fully Substituted 1,2-Diaminoimidazoles
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- 作者：Orazio A. Attanasi ; Silvia Bartoccini ; Gianfranco Favi ; Paolino Filippone ; Francesca Romana Perrulli ; Stefania Santeusanio
- 刊名：The Journal of Organic Chemistry
- 出版年：2012
- 出版时间：October 19, 2012
- 年：2012
- 卷：77
- 期：20
- 页码：9338-9343
- 全文大小：230K
- 年卷期：v.77,no.20(October 19, 2012)
- ISSN：1520-6904
文摘
One-pot sequential aza-Michael, Staudinger, and aza-Wittig reactions on 1,2-diaza-1,2-dienes (DDs) can afford fully substituted 1,2-diaminoimidazoles. A plausible mechanism for the imidazole core formation involving an intramolecular ring closure of the carbodiimide-derived phosphazene intermediate is given. The reported strategy has sufficient flexibility to allow substituted 1,2-diaminoimidazoles with orthogonal nitrogen-protective groups to be generated from a variety of heterocumulene moieties linked to the DDs skeleton.